(E)-Stilbene

For the class of antioxidant compounds that share the same chemical skeleton, see stilbenoid.
(E)-Stilbene
trans-stilbene - skeletal formula
trans-stilbene - ball-and-stick model
Names
IUPAC name
(E)-Stilbene[1]
Preferred IUPAC name
1,1′-[(E)-Ethene-1,2-diyl]dibenzene[1]
Other names
Bibenzylidene
trans-α,β-Diphenylethylene
(E)-1,2-Diphenylethylene
((1E)-2-Phenylvinyl)benzene
trans-Stilbene
[(E)-2-Phenylethenyl]benzene
Identifiers
3D model (JSmol)
1616740
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.817 Edit this at Wikidata
EC Number
  • 203-098-5
4381
UNII
UN number 3077
  • InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11+ checkY
    Key: PJANXHGTPQOBST-VAWYXSNFSA-N checkY
  • InChI=1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11+
    Key: PJANXHGTPQOBST-VAWYXSNFBV
  • c2(\C=C\c1ccccc1)ccccc2
  • c1ccc(cc1)/C=C/c2ccccc2
Properties
C14H12
Molar mass 180.250 g·mol−1
Appearance Solid
Density 0.9707 g/cm3
Melting point 122 to 125 °C (252 to 257 °F; 395 to 398 K)
Boiling point 305 to 307 °C (581 to 585 °F; 578 to 580 K)
Practically insoluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point > 112 °C (234 °F; 385 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

(E)-Stilbene, commonly known as trans-stilbene, is an organic compound represented by the condensed structural formula C6H5CH=CHC6H5. Classified as a diarylethene, it features a central ethylene moiety with one phenyl group substituent on each end of the carbon–carbon double bond. It has an (E) stereochemistry, meaning that the phenyl groups are located on opposite sides of the double bond, the opposite of its geometric isomer, cis-stilbene. Trans-stilbene occurs as a white crystalline solid at room temperature and is highly soluble in organic solvents. It can be converted to cis-stilbene photochemically, and further reacted to produce phenanthrene.

Stilbene was discovered in 1843 by the French chemist Auguste Laurent.[2] The name "stilbene" is derived from the Greek word στίλβω (stilbo), which means "I shine", on account of the lustrous appearance of the compound.[3]

  1. ^ a b International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 379. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Laurent, Auguste (1843). "Mémoire sur la série stilbique" [Memoir on the stilbene series]. Comptes rendus (in French). 16: 856–860. From p. 857: "En soumettant ce sulfure à la distillation, il donne plusieurs produits, et entre autres, un composé fort remarquable que je nomme stilbène." (On submitting this sulfide [i.e., phenyl thioaldehyde, C6H5(CS)H] to [dry] distillation, it gives several products, and among others, a very remarkable compound which I name "stilbene".)
  3. ^ Miller, William Allen (1880). Elements of Chemistry: Theoretical and Practical. Vol. 3 (5th ed.). London, England: Longmans, Green and Co. p. 366.